EP2083026A2 - Polyuréthane thermoplastique et son utilisation - Google Patents

Polyuréthane thermoplastique et son utilisation Download PDF

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Publication number
EP2083026A2
EP2083026A2 EP09000324A EP09000324A EP2083026A2 EP 2083026 A2 EP2083026 A2 EP 2083026A2 EP 09000324 A EP09000324 A EP 09000324A EP 09000324 A EP09000324 A EP 09000324A EP 2083026 A2 EP2083026 A2 EP 2083026A2
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EP
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Prior art keywords
thermoplastic polyurethane
molecular weight
tpu
optionally
mol
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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EP09000324A
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German (de)
English (en)
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EP2083026A3 (fr
Inventor
Henricus Dr. Peerlings
Juergen Winkler
Faisal Dr. Shafiq
Markus Broich
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Covestro Deutschland AG
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Bayer MaterialScience AG
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Publication of EP2083026A2 publication Critical patent/EP2083026A2/fr
Publication of EP2083026A3 publication Critical patent/EP2083026A3/fr
Withdrawn legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/61—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/4009—Two or more macromolecular compounds not provided for in one single group of groups C08G18/42 - C08G18/64
    • C08G18/4018—Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3203—Polyhydroxy compounds
    • C08G18/3206—Polyhydroxy compounds aliphatic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4833—Polyethers containing oxyethylene units
    • C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
    • C08G18/485—Polyethers containing oxyethylene units and other oxyalkylene units containing mixed oxyethylene-oxypropylene or oxyethylene-higher oxyalkylene end groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6633—Compounds of group C08G18/42
    • C08G18/6637—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/664—Compounds of group C08G18/42 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6666—Compounds of group C08G18/48 or C08G18/52
    • C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/6674—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/3203
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • C08L75/06—Polyurethanes from polyesters

Definitions

  • the present invention relates to thermoplastic polyurethane molding compositions with improved surface resistance (writing and scratch resistance) and good technical processability and their use.
  • TPU Thermoplastic polyurethanes
  • TPUs are usually composed of linear polyols (macrodiols), such as polyester, polyether or polycarbonate diols, organic diisocyanates and short-chain, mostly difunctional alcohols (chain extenders). They can be produced continuously or discontinuously.
  • the best known production methods are the strip method ( GB-A 1 057 018 ) and the extruder process ( DE-A 19 64 834 ).
  • thermoplastically processable polyurethane elastomers can be carried out either stepwise (Prepolymerdosier boulder) or by the simultaneous reaction of all components in one step (one-shot dosing).
  • DE-A 102 30 020 describes the use of polyorganosiloxanes to improve scratch and scratch resistance (mechanical surface resistance) for TPUs.
  • scratch and scratch resistance mechanical surface resistance
  • the object of the present invention was therefore to provide thermoplastic polyurethanes (TPU) which have improved mechanical surface resistance and at the same time have good industrial processability and no surface defects during processing.
  • TPU thermoplastic polyurethanes
  • organic diisocyanates it is possible to use aliphatic, cycloaliphatic, araliphatic, aromatic and heterocyclic diisocyanates or any desired mixtures of these diisocyanates (cf. HOUBEN-WEYL "Methods of Organic Chemistry", Volume E20 “Macromolecular Materials”, Georg Thieme Verlag, Stuttgart, New York 1987, pp. 1587-1593 or Justus Liebigs Annalen der Chemie, 562, pages 75 to 136 ).
  • aliphatic diisocyanates such as ethylene diisocyanate, 1,4-tetramethylene diisocyanate, 1,6-hexamethylene diisocyanate, 1,12-dodecane diisocyanate
  • cycloaliphatic diisocyanates such as isophorone diisocyanate, 1,4-cyclohexane diisocyanate, 1-methyl-2,4-cyclohexane diisocyanate and 1-methyl-2,6-cyclohexane diisocyanate and the corresponding isomer mixtures, 4,4'-dicyclohexylmethane diisocyanate, 2,4'-dicyclohexylmethane diisocyanate and 2 , 2'-Dicyclohexylmethandiisocyanat and the corresponding isomer mixtures; also aromatic diisocyanates, such as 2,4-tolylene diisocyanate, mixtures of 2,4-tolylene diisocyanate and
  • the diisocyanates mentioned can be used individually or in the form of mixtures with one another.
  • polyisocyanates can also be used together with up to 15 mol% (calculated on the total diisocyanate) of a polyisocyanate, but it must be added at most as much polyisocyanate that a still melt-processable product is formed.
  • polyisocyanates are triphenylmethane-4,4 ', 4 "-triisocyanate and polyphenyl-polymethylene-polyisocyanates.
  • the chain extenders b) preferably have on average 1.8 to 3.0 Zerewitinoff-active hydrogen atoms and have a molecular weight of 60 to 400. These are preferably understood as meaning those having two to three, more preferably having two hydroxyl groups.
  • chain extender b) one or more compounds are preferably used from the group of aliphatic diols having 2 to 14 carbon atoms, such as, for example, ethanediol, 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, 2,3-butanediol , 1,5-pentanediol, 1,6-hexanediol, diethylene glycol, dipropylene glycol, 1,4-cyclohexanediol, 1,4-dimethanolcyclohexane and neopentyl glycol.
  • aliphatic diols having 2 to 14 carbon atoms such as, for example, ethanediol, 1,2-propanediol, 1,3-propanediol, 1,4-butanediol, 2,3-butanediol , 1,5-pentanediol,
  • diesters of terephthalic acid with glycols having 2 to 4 carbon atoms for example terephthalic acid-bis-ethylene glycol or terephthalic acid bis-1,4-butanediol, hydroxyalkylene ethers of hydroquinone, for example 1,4-di ( ⁇ -hydroxyethyl) hydroquinone, Ethoxylated bisphenols, for example 1,4-di ( ⁇ -hydroxyethyl) bisphenol A.
  • polyol component c) are those having an average of at least 1.8 to at most 3.0 Zerewitinoff-active hydrogen atoms and a number average molecular weight M n used from 450 to 10,000. Due to production, the polyols often contain small amounts of non-linear compounds. Therefore, one often speaks of "substantially linear polyols". Preference is given to polyester, polyether, polycarbonate diols or mixtures of these.
  • two to three, preferably two hydroxyl-containing compounds are preferred, especially those with number average molecular weights M n from 450 to 6,000, more preferably those with number average molecular weights M n from 600 to 4,500; Hydroxyl-containing polyesters, polyethers and polycarbonates are particularly preferred.
  • Suitable polyether diols can be prepared by reacting one or more alkylene oxides having 2 to 4 carbon atoms in the alkylene radical with a starter molecule containing two active hydrogen atoms bonded.
  • alkylene oxides which may be mentioned are: ethylene oxide, 1,2-propylene oxide, epichlorohydrin and 1,2-butylene oxide and 2,3-butylene oxide.
  • Preferably used are ethylene oxide, propylene oxide and mixtures of 1,2-propylene oxide and ethylene oxide.
  • the alkylene oxides can be used individually, alternately in succession or as mixtures.
  • starter molecules are: water, amino alcohols, such as N-alkyldiethanolamines, for example N-methyldiethanolamine and diols, such as ethylene glycol, 1,3-propylene glycol, 1,4-butanediol and 1,6-hexanediol.
  • Suitable polyether polyols are also the hydroxyl-containing polymerization of tetrahydrofuran. It is also possible to use trifunctional polyethers in proportions of from 0 to 30% by weight, based on the bifunctional polyethers, but at most in such an amount that a still thermoplastically processable product is formed.
  • the substantially linear polyether diols preferably have number average molecular weights M n from 450 to 6,000. They can be used both individually and in the form of mixtures with one another.
  • Suitable polyester diols can be prepared, for example, from dicarboxylic acids having 2 to 12 carbon atoms, preferably 4 to 6 carbon atoms, and polyhydric alcohols.
  • Suitable dicarboxylic acids are, for example: aliphatic dicarboxylic acids, such as succinic acid, glutaric acid, adipic acid, suberic acid, azelaic acid and sebacic acid, or aromatic dicarboxylic acids, such as phthalic acid, isophthalic acid and terephthalic acid.
  • the dicarboxylic acids can be used individually or as mixtures, for example in the form of an amber, glutaric and adipic acid mixture.
  • polyester diols it may optionally be advantageous, instead of the dicarboxylic acids, to use the corresponding dicarboxylic acid derivatives, such as carboxylic acid diesters to use with 1 to 4 carbon atoms in the alcohol radical, carboxylic anhydrides or carboxylic acid chlorides.
  • dicarboxylic acids such as carboxylic acid diesters to use with 1 to 4 carbon atoms in the alcohol radical, carboxylic anhydrides or carboxylic acid chlorides.
  • polyhydric alcohols examples include glycols having 2 to 10, preferably 2 to 6 carbon atoms, for example ethylene glycol, diethylene glycol, 1,4-butanediol, 1,5-pentanediol, 1,6-hexanediol, 1,10-decanediol, 2,2- Dimethyl-1,3-propanediol, 1,3-propanediol or dipropylene glycol.
  • the polyhydric alcohols may be used alone or mixed with each other.
  • esters of carbonic acid with the diols mentioned in particular those having 4 to 6 carbon atoms, such as 1,4-butanediol or 1,6-hexanediol, condensation products of ⁇ -hydroxycarboxylic acids, such as ⁇ -hydroxycaproic acid or polymerization of lactones, for example optionally substituted ⁇ -caprolactones.
  • Ethanediol polyadipates, 1,4-butanediol polyadipates, ethanediol-1,4-butanediol polyadipates, 1,6-hexanediol neopentyl glycol polyadipates, 1,6-hexanediol-1,4-butanediol polyadipates and polycaprolactones are preferably used as polyester diols.
  • the polyester diols have number average molecular weights M n from 450 to 10,000 and can be used individually or in the form of mixtures with one another.
  • polyorganosiloxanes d) are compounds of the general formula (R 2 SiO) n , wherein R represents an organic hydrocarbon radical which may be constructed both linear and branched, and having 1 to 27 carbon atoms. Of the repeat units there are at least 3 and at most 6,000.
  • the polyorganosiloxanes d1) and d2) can be added in bulk or as a masterbatch in a vehicle.
  • Suitable carrier substances are thermoplastic elastomers, for example polyether esters, polyester esters, TPU, styrene-ethylene-butadiene-styrene (SEBS), acrylonitrile-butadiene-styrene (ABS), styrene-acrylonitrile (SAN), polyamide (PA), acrylate Styrene-acrylate block copolymer (ASA), polybutylene terephthalate (PBT), polycarbonate (PC), polyether block amide (PEBA), polymethyl methacrylate (PMMA), polyoxymethylene (POM) or polyvinyl chloride (PVC).
  • polyether esters for example polyether esters, polyester esters, TPU, styrene-ethylene-butadiene-styrene (SEBS), acrylonitrile-butadiene-styrene (ABS), styrene-acrylonitrile (SAN), polyamide (PA), acrylate Styrene-
  • the polyorganosiloxane can already be used in the production of the TPU TPU raw materials or subsequently the finished TPU, e.g. be added by compounding.
  • the relative amounts of the Zerewitinoff active compounds are preferably selected such that the ratio of the number of isocyanate groups to the number of isocyanate-reactive groups is 0.9: 1 to 1.1: 1.
  • Suitable catalysts e) are the tertiary amines known and customary in the prior art, for example triethylamine, dimethylcyclohexylamine, N-methylmorpholine, N, N'-dimethylpiperazine, 2- (dimethylaminoethoxy) ethanol, diazabicyclo [2,2,2 ] octane and the like, and in particular organic metal compounds such as titanic acid esters, iron compounds, bismuth compounds or tin compounds such as tin diacetate, tin dioctoate, tin dilaurate or Zinndialkylsalze aliphatic carboxylic acids such as dibutyltin diacetate or dibutyltin dilaurate or the like.
  • Preferred catalysts are organic metal compounds, in particular titanic acid esters, iron, tin, zirconium and bismuth compounds.
  • the total amount of catalysts in the TPU according to the invention is generally preferably 0 to 5 wt .-%, preferably 0 to 2 wt .-%, based on the total amount of TPU.
  • the thermoplastic polyurethanes of the invention may contain auxiliaries and additives f).
  • auxiliaries and additives are lubricants and mold release agents, such as fatty acid esters, their metal soaps, fatty acid amides, fatty acid ester amides, antiblocking agents, flameproofing agents, plasticizers (as described, for example, in US Pat M. Szycher in M.
  • thermoplastics for example polycarbonates and acrylonitrile / butadiene / styrene terpolymers (ABS), in particular ABS.
  • ABS acrylonitrile / butadiene / styrene terpolymers
  • elastomers such as rubber, ethylene / vinyl acetate copolymers, styrene / butadiene copolymers and other TPU's can also be used.
  • auxiliaries and additives f) can take place during the production process of the TPU and / or during an additional compounding of the TPU.
  • Monofunctional compounds which react with isocyanates can be used in amounts of up to 2% by weight, based on TPU, as what are known as chain terminators g).
  • Suitable examples are monoamines, such as butyl and dibutylamine, octylamine, stearylamine, N-methylstearylamine, pyrrolidine, piperidine or cyclohexylamine, monoalcohols such as butanol, 2-ethylhexanol, octanol, dodecanol, stearyl alcohol, the various amyl alcohols, cyclohexanol and ethylene glycol monomethyl ether.
  • the TPUs according to the invention are preferably used by injection molding, extrusion processes and / or powder-slush processes.
  • the TPUs according to the invention are preferably used for the production of heat-resistant molded parts and skins with good mechanical surface resistance.
  • the TPU be used for the interior of motor vehicles.
  • TPU-1 Preparation of an aromatic TPU (TPU-1):
  • TPU-2 aliphatic TPU
  • a mixture of 500 g PE 225B, 214 g Acclaim ® 2220N, 91 g HDO, 5 g Irganox ® 1010 5 g Tinuvin ® 234 and 50 ppm of DBTL (based on the amount of polyol) was stirred with a paddle at a speed of 500 Revolutions per minute (rpm) to 130 ° C heated. Thereafter, 183 g of HDI were added. The mixture was then stirred until the maximum possible increase in viscosity and then the TPU poured out. The material was 30 min. thermally treated at 80 ° C and then granulated. This material was used as the base material for Examples 4 to 9.
  • Example 1 an aromatic TPU (TPU-1) was used. Without polyorganosiloxane (Example 1), the surface resistance is poor. While using high molecular weight polyorganosiloxane (Example 2), the result from the Crockmeter test was good, but the scratch test was failed. The TPU from Example 3 met all surface sensitivity requirements and achieved good industrial processability.
  • Example 4 an aliphatic TPU (TPU-2) was used.
  • TPU-2 aliphatic TPU
  • Comparative Examples 4, 5 and 9 no polyorganosiloxane (Example 4), only a high molecular weight polyorganosiloxane (Example 5) or only a low molecular weight polyorganosiloxane (Example 9) were used.
  • the TPUs of Examples 4 and 9 showed a poor scratch test result.
  • Example 9 there were also feed problems in the hopper of the injection molding machine.
  • the material from example 5 had a good surface resistance, but showed problems in the technical processability.
  • TPUs of Examples 6 to 8 according to the invention met all surface sensitivity requirements and exhibited good industrial processability.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Laminated Bodies (AREA)
EP09000324A 2008-01-25 2009-01-13 Polyuréthane thermoplastique et son utilisation Withdrawn EP2083026A3 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE102008006004A DE102008006004B3 (de) 2008-01-25 2008-01-25 Thermoplastische Polyurethane und deren Verwendung

Publications (2)

Publication Number Publication Date
EP2083026A2 true EP2083026A2 (fr) 2009-07-29
EP2083026A3 EP2083026A3 (fr) 2010-01-27

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Country Status (10)

Country Link
US (1) US20090192274A1 (fr)
EP (1) EP2083026A3 (fr)
JP (1) JP2009173932A (fr)
KR (1) KR20090082153A (fr)
CN (1) CN101492526A (fr)
AT (1) ATE551372T1 (fr)
AU (1) AU2009200182A1 (fr)
BR (1) BRPI0900140A2 (fr)
CA (1) CA2650697A1 (fr)
DE (1) DE102008006004B3 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP2383305A1 (fr) 2010-04-28 2011-11-02 Bayer MaterialScience AG Polyuréthanes thermoplastiques et leur utilisation
WO2011140068A1 (fr) * 2010-05-07 2011-11-10 Ppg Industries Ohio, Inc. Compositions filmogènes durcissables possédant des propriétés d'auto-réparation
EP2586807A1 (fr) 2011-10-25 2013-05-01 Bayer Intellectual Property GmbH Polyuréthane thermoplastique et son utilisation

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DE102013113320B4 (de) 2013-12-02 2019-11-14 Timur Ünlü Verwendung einer pulverförmigen Zusammensetzung aus thermoplastischem Polyurethan und Verfahren zur Herstellung eines Formkörpers
CH710441A2 (de) 2014-12-02 2016-06-15 Rowak Ag Pulverförmige Zusammensetzungen aus thermoplastischen Kunststoffen und Verwendung der Zusammensetzungen.
KR102223669B1 (ko) * 2016-07-13 2021-03-05 와커 헤미 아게 실록산-오르가노-공중합체를 함유하는 중합체 조성물

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GB1057018A (en) 1964-12-14 1967-02-01 Ici Ltd Polyurethane polymers
DE1964834A1 (de) 1969-12-24 1971-07-01 Bayer Ag Verfahren zur Herstellung von Polyurethan-Elastomeren
DE2901774A1 (de) 1979-01-18 1980-07-24 Elastogran Gmbh Rieselfaehiges, mikrobenbestaendiges farbstoff- und/oder hilfsmittelkonzentrat auf basis eines polyurethan-elastomeren und verfahren zu seiner herstellung
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US20090192274A1 (en) 2009-07-30
DE102008006004B3 (de) 2009-08-27
BRPI0900140A2 (pt) 2009-09-15
JP2009173932A (ja) 2009-08-06
CA2650697A1 (fr) 2009-07-25
ATE551372T1 (de) 2012-04-15

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